CN103943784A - Organic light-emitting device - Google Patents
Organic light-emitting device Download PDFInfo
- Publication number
- CN103943784A CN103943784A CN201410182230.4A CN201410182230A CN103943784A CN 103943784 A CN103943784 A CN 103943784A CN 201410182230 A CN201410182230 A CN 201410182230A CN 103943784 A CN103943784 A CN 103943784A
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- CN
- China
- Prior art keywords
- replacement
- organic light
- light emitting
- emitting apparatus
- independently
- Prior art date
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- IYZMXHQDXZKNCY-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n,4-n-bis[4-(n-phenylanilino)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IYZMXHQDXZKNCY-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- YMMGRPLNZPTZBS-UHFFFAOYSA-N 2,3-dihydrothieno[2,3-b][1,4]dioxine Chemical compound O1CCOC2=C1C=CS2 YMMGRPLNZPTZBS-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- UPSWHSOSMRAWEH-UHFFFAOYSA-N 2-n,3-n,4-n-tris(3-methylphenyl)-1-n,1-n,2-n,3-n,4-n-pentakis-phenylbenzene-1,2,3,4-tetramine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=C(N(C=3C=CC=CC=3)C=3C=C(C)C=CC=3)C(N(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 UPSWHSOSMRAWEH-UHFFFAOYSA-N 0.000 description 1
- NSMJMUQZRGZMQC-UHFFFAOYSA-N 2-naphthalen-1-yl-1H-imidazo[4,5-f][1,10]phenanthroline Chemical compound C12=CC=CN=C2C2=NC=CC=C2C2=C1NC(C=1C3=CC=CC=C3C=CC=1)=N2 NSMJMUQZRGZMQC-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 1
- OSQXTXTYKAEHQV-WXUKJITCSA-N 4-methyl-n-[4-[(e)-2-[4-[4-[(e)-2-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(\C=C\C=2C=CC(=CC=2)C=2C=CC(\C=C\C=3C=CC(=CC=3)N(C=3C=CC(C)=CC=3)C=3C=CC(C)=CC=3)=CC=2)=CC=1)C1=CC=C(C)C=C1 OSQXTXTYKAEHQV-WXUKJITCSA-N 0.000 description 1
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 1
- JEGZRTMZYUDVBF-UHFFFAOYSA-N Benz[a]acridine Chemical compound C1=CC=C2C3=CC4=CC=CC=C4N=C3C=CC2=C1 JEGZRTMZYUDVBF-UHFFFAOYSA-N 0.000 description 1
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000001545 azulenes Chemical class 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940126540 compound 41 Drugs 0.000 description 1
- 229940125936 compound 42 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 238000002484 cyclic voltammetry Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- DDTGNKBZWQHIEH-UHFFFAOYSA-N heptalene Chemical compound C1=CC=CC=C2C=CC=CC=C21 DDTGNKBZWQHIEH-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- QSQIGGCOCHABAP-UHFFFAOYSA-N hexacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC6=CC=CC=C6C=C5C=C4C=C3C=C21 QSQIGGCOCHABAP-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000005054 naphthyridines Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- GUVXZFRDPCKWEM-UHFFFAOYSA-N pentalene Chemical compound C1=CC2=CC=CC2=C1 GUVXZFRDPCKWEM-UHFFFAOYSA-N 0.000 description 1
- NQFOGDIWKQWFMN-UHFFFAOYSA-N phenalene Chemical compound C1=CC([CH]C=C2)=C3C2=CC=CC3=C1 NQFOGDIWKQWFMN-UHFFFAOYSA-N 0.000 description 1
- 150000005053 phenanthridines Chemical class 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000000644 propagated effect Effects 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/805—Electrodes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
- H10K50/856—Arrangements for extracting light from the devices comprising reflective means
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
Landscapes
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention refers to an organic light-emitting device including a substrate; a first electrode on the substrate; a second electrode; an organic layer between the first electrode and the second electrode, the organic layer including an emission layer; and a first layer including a cyano group-containing compound, the first layer being between the first electrode and the emission layer, wherein the first electrode includes an Al-based reflective layer and a transparent conductive layer sequentially stacked on the substrate, the Al-based reflective layer including a first element and nickel (Ni), and the first element includes at least one of lanthanum (La), cerium (Ce), praseodymium (Pr), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), and lutetium (Lu).
Description
The application is to be on October 12nd, 2010 applying date, and application number is 201010513076.6, and what denomination of invention was the application for a patent for invention of " organic light emitting apparatus " divides an application.
Technical field
Each execution mode of the present invention relates to organic light emitting apparatus.
Background technology
Organic light emitting apparatus (OLED) is selfluminous device, has the advantages such as driving voltage characteristic such as wide visual angle, excellent contrast, quick response, high brightness, excellence, and multicolor image can be provided.
OLED has and comprises for example substrate, and stacks gradually anode, hole transmission layer (HTL), luminescent layer (EML), electron transfer layer (ETL) and negative electrode on this substrate.<0} is at this, and HTL, EML and ETL can be the organic film for example being formed by organic compound.
The operating principle of OLED with said structure is as follows.
When antianode and negative electrode apply voltage, by anode injected holes, can move to EML by HTL; And can move to EML by ETL by negative electrode injected electrons.Hole and electrons at EML again in conjunction with to produce exciton.When exciton drops to ground state by excitation state, can be luminous.
Summary of the invention
The application's the embodiments of the present invention relate to a kind of organic light emitting apparatus, and described organic light emitting apparatus has overcome the one or more problems that cause because of the restriction of prior art and shortcoming substantially.
The feature of embodiment of the present invention is to provide the organic light emitting apparatus with excellent driving voltage characteristic and excellent power efficiency characteristic was.
At least one in above and other feature and advantage can be by providing organic light emitting apparatus to realize, and described organic light emitting apparatus comprises: substrate; The first electrode on described substrate; The second electrode; Organic layer between described the first electrode and the second electrode, described organic layer comprises luminescent layer; With the ground floor that comprises the compound of cyano-containing, described ground floor is between described the first electrode and described luminescent layer, wherein said the first electrode comprises Al class reflector and the transparency conducting layer stacking gradually on described substrate, described Al class reflector comprises the first element and nickel (Ni), and described the first element comprises at least one in lanthanum (La), cerium (Ce), praseodymium (Pr), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb) and lutetium (Lu).
Described the first electrode can further comprise the zinc oxide film containing the second element, and described the second element comprises at least one in aluminium (Al), indium (In), gallium (Ga), germanium (Ge), gadolinium (Gd), zirconium (Zr), molybdenum (Mo) and nickel (Ni).
Described Al class reflector, described transparency conducting layer and the described zinc oxide film that contains the second element can these sequentially stack gradually on described substrate.
The described zinc oxide film that contains the second element based on 100 weight portions, the content of described the second element can be approximately 0.5 to approximately 10 weight portion.
Described Al class reflector can comprise La, Ni and Al.
The compound of described cyano-containing can comprise any in the compound of general formula 1 to 20 expression:
In general formula 1 to 20,
X
1to X
4a kind of expression in general formula 30A to 30D independently of one another;
Y
1to Y
8can be N or C (R independently of one another
103);
Z
1to Z
4can be C or N independently of one another;
A
1and A
2can be independently of one another-O-,-S-,-N (R
104) or C (R
105) (R
106)-;
Q
101and Q
102can be C independently of one another
2~C
10alkylidene, C
2~C
10alkenylene, or by halogen atom, cyano group, hydroxyl, C
1~C
10alkyl or C
1~C
10the C that replaces of alkoxyl
2~C
10alkylidene or C
2~C
10alkenylene;
T
1and T
2can be C independently of one another
5~C
30aromatic ring system, C
2~C
30hetero-aromatic ring system, or by halogen atom, cyano group, hydroxyl, C
1~C
10alkyl or C
1~C
10the C that replaces of alkoxyl
5~C
30aromatic ring system or C
2~C
30hetero-aromatic ring system;
P can be 1 to 10 integer;
Q can be 0 to 10 integer;
R
101to R
106can be hydrogen atom independently of one another, halogen atom, cyano group, hydroxyl, C
1~C
10alkyl, C
1~C
10alkoxyl, by halogen atom, cyano group, hydroxyl, C
5~C
14aryl and C
2~C
14heteroaryl in the C of at least one replacement
1~C
10alkyl, by halogen atom, cyano group, hydroxyl, C
5~C
14aryl, C
2~C
14heteroaryl in the C of at least one replacement
1~C
10alkoxyl,
or-N (R
107) (R
108); R
107and R
108be hydrogen atom, C independently of one another
1~C
10alkyl, phenyl or xenyl; And
L
101can be C
5~C
14arlydene, C
5~C
14heteroarylidene, and by halogen atom, cyano group, hydroxyl, C
1~C
10alkyl and C
1~C
10alkoxyl in the C of at least one replacement
5~C
14arlydene or C
5~C
14heteroarylidene:
X
1to X
4can be the compound being represented by general formula 30A or 30D independently of one another.
R
103can be hydrogen atom, halogen atom, cyano group, C
1~C
10alkyl, C
1~C
10alkoxyl, by the C of at least one replacement in halogen atom, cyano group, phenyl, naphthyl, anthryl, pyridine radicals, thiophenyl and benzo thiophenyl
1~C
10alkyl or C
1~C
10alkoxyl, or-N (R
107) (R
108) in a kind of, R wherein
107and R
108can be hydrogen atom, C independently of one another
1~C
10alkyl, phenyl or xenyl.
R
101and R
102can be independently of one another cyano group,
A
1and A
2in each can be-S-.
Q
101and Q
102can be ethylidene independently of one another, propylidene, ethenylidene, allylidene, by the ethylidene of at least one replacement in halogen atom, cyano group, hydroxyl, by the propylidene of at least one replacement in halogen atom, cyano group, hydroxyl, by the ethenylidene of at least one replacement in halogen atom, cyano group, hydroxyl, or by the allylidene of at least one replacement in halogen atom, cyano group, hydroxyl.
T
1and T
2can be benzene independently of one another, naphthalene, anthracene, thiophene, thiadiazole , oxadiazole, or be by halogen atom, cyano group, C
1~C
10alkyl and C
1~C
10alkoxyl in benzene, naphthalene, anthracene, thiophene, the thiadiazole Huo oxadiazole of at least one replacement.
P can be 1.
Q can be 0,1 or 2.
L
101can be sub-thiophenyl, the sub-thiophenyl of benzo, by halogen atom, cyano group and C
1~C
10alkyl in the sub-thiophenyl of at least one replacement, with by halogen atom, cyano group and C
1~C
10alkyl in the sub-thiophenyl of benzo of at least one replacement in a kind of.
Can the serve as reasons compound of any expression in following general formula 1A to 20B of the compound of described cyano-containing:
Wherein, R
103and R
109can be hydrogen atom ,-F, cyano group, methyl, ethyl, propyl group, vinyl, methoxyl group, ethyoxyl or propoxyl group independently of one another.
Described ground floor can further comprise hole transport compound.
Described hole transport compound can comprise by following general formula 41 or 42 compounds that represent:
Wherein, R
10can be by-(Ar
1)
n-Ar
2represent;
R
16can be by-(Ar
11)
m-Ar
12represent;
Ar
1, Ar
11, L
1and L
11can be independently of one another for replacing or unsubstituted C
1~C
30alkylidene, replacement or unsubstituted C
2~C
30alkenylene, replacement or unsubstituted C
5~C
30arlydene, replacement or unsubstituted C
4~C
30heteroarylidene or by-N (Q
1the group of)-represent;
N, m, a and b can be 0 to 10 integer independently of one another.
R
1to R
3, R
11to R
15, R
17, R
18, R
21to R
29, Ar
2, Ar
12and Q
1can be hydrogen atom, halogen atom, hydroxyl, cyano group, replacement or unsubstituted C independently of one another
1~C
30alkyl, replacement or unsubstituted C
2~C
30thiazolinyl, replacement or unsubstituted C
2~C
30alkynyl, replacement or unsubstituted C
1~C
30alkoxyl, replacement or unsubstituted C
1~C
30alkylthio group, replacement or unsubstituted C
5~C
30aryl, C
4~C
30heteroaryl or by-N (Q
2) (Q
3) group that represents; And
Q
2and Q
3can be hydrogen atom, halogen atom, hydroxyl, cyano group, replacement or unsubstituted C independently of one another
1~C
30alkyl, replacement or unsubstituted C
2~C
30thiazolinyl, replacement or unsubstituted C
2~C
30alkynyl, replacement or unsubstituted C
1~C
30alkoxyl, replacement or unsubstituted C
1~C
30alkylthio group, replacement or unsubstituted C
5~C
30aryl or replacement or unsubstituted C
4~C
30heteroaryl,
Wherein-(Ar
1)
n-in n Ar
1base is same to each other or different to each other ,-(Ar
11)
m-in m Ar
11base is same to each other or different to each other ,-(L
1)
a-in a L
1base is same to each other or different to each other, and-(L
11)
b-in b L
11base is same to each other or different to each other.
Ar
1and Ar
11can be C independently of one another
1~C
10alkylidene, phenylene, naphthylene, anthrylene, fluorenylidene, sub-carbazyl, sub-pyrazolyl, sub-pyridine radicals, sub-triazine radical ,-N (Q
1)-, or by halogen atom, cyano group, hydroxyl, C
1~C
10alkyl, C
1~C
10alkoxyl, phenyl, naphthyl and anthryl in the C of at least one replacement
1~C
10alkylidene, phenylene, naphthylene, anthrylene, fluorenylidene, sub-carbazyl, sub-pyrazolyl, sub-pyridine radicals or sub-triazine radical; And Q wherein
1can be hydrogen atom, C
1~C
10alkyl, C
1~C
10alkoxyl, phenyl, naphthyl, carbazyl, fluorenyl, pyrenyl, selected free halogen atom, cyano group, hydroxyl, C
1~C
10alkyl, C
1~C
10alkoxyl, phenyl, naphthyl and the C that replaces of at least one substituting group in the group that forms of anthryl
1~C
10alkyl, C
1~C
10alkoxyl, phenyl, naphthyl, carbazyl, fluorenyl or pyrenyl, or-N (Q
2) (Q
3) in a kind of.
Ar
2and Ar
12can be hydrogen atom independently of one another, C
1~C
10alkyl, phenyl, naphthyl, carbazyl, fluorenyl, pyrenyl, by halogen atom, cyano group, hydroxyl, C
1~C
10alkyl, C
1~C
10alkoxyl, phenyl, naphthyl and anthryl in the C of at least one replacement
1~C
10alkyl, C
1~C
10alkoxyl, phenyl, naphthyl, carbazyl, fluorenyl or pyrenyl, or-N (Q
2) (Q
3), and Q wherein
2and Q
3can be hydrogen atom, methyl, ethyl, phenyl, tolyl, xenyl, naphthyl or first naphthyl independently of one another.
N and m can be 0,1,2,3,4,5 or 6 independently of one another.
Described ground floor based on 100 weight portions, the content of the compound of cyano-containing described in described ground floor can be approximately 0.1 to approximately 20 weight portion.
Described ground floor can have approximately
extremely approximately
thickness.
Distance between described ground floor and described luminescent layer can be approximately
or larger.
Described organic light emitting apparatus can further comprise at least one of hole injection layer and hole transmission layer between described ground floor and described luminescent layer.
Described Al class reflector can comprise Al
xni phase, and x can be approximately 2.5 to approximately 3.5.
Described Al class reflector can comprise Al
xni phase, and can contact described transparency conducting layer, wherein said Al
xni mutually middle x is approximately 2.5 to approximately 3.5.
X can be 3.
Described organic light emitting apparatus can further comprise rich nickel (Ni) oxide skin(coating) in described Al class reflector on the surface of described transparency conducting layer.
In described Al class reflector, the content of nickel (Ni) can be about 0.6wt% to about 5wt%.
Described the first element can comprise lanthanum (La).
The content of the first element described in described Al class reflector can be about 0.1wt% to about 3wt%.
Described transparency conducting layer can comprise tin indium oxide (ITO) or tin oxide (SnO
2).
Accompanying drawing explanation
By with reference to accompanying drawing detailed description exemplary execution mode, above and other feature and advantage will become more apparent to those of ordinary skills, wherein:
Fig. 1 shows according to the sectional view of the organic light emitting apparatus of an execution mode (OLED) structure;
Fig. 2 A shows transmission electron microscope (TEM) image according to the cross section in the aluminium of an execution mode (Al) class reflector;
Fig. 2 B shows scanning transmission electron microscope (STEM)-angle of elevation ring-type darkfield image of the aluminium shown in Fig. 2 A (Al) based reflection film;
Fig. 2 C shows the result about the X-ray energy dispersion spectrum of the irregular grown crystal in Fig. 2 A;
Fig. 3 shows according to the TEM image of the cross section of the first electrode of another execution mode; With
Fig. 4 shows according to the sectional view of the OLED structure of another execution mode.
Embodiment
The korean patent application 10-2009-0096822 integral body that by reference name that in October, 2009,12Xiang Korea S Department of Intellectual Property submitted to is called to " organic light emitting apparatus " at this is herein incorporated.
Hereinafter with reference to accompanying drawing illustrated example execution mode more completely; Yet, described execution mode can be various different modes implement, and should not be construed as and be limited to execution mode as herein described.Or rather, provide these execution modes to make the disclosure complete and complete, and scope of the present invention is intactly conveyed to those skilled in the art.
In the accompanying drawings, for the clearness illustrating, the size in layer and region can be amplified.What will also be understood that is when certain one deck or element b referred to as " on another layer or substrate ", it can be directly on this another layer or substrate, or also can there is insert layer.In addition, it will also be appreciated that when certain one deck is known as " between two-layer ", it can be this only one deck between two-layer, or also can have one or more insert layers.In full, similar Reference numeral represents similar components.
Fig. 1 shows according to the schematic cross-section of the organic light emitting apparatus of an execution mode (OLED) 10.With reference to Fig. 1, according to the OLED10 of present embodiment, can comprise substrate 1, the first electrode 5, the ground floor 6 that comprises the compound of cyano-containing, organic layer 7 and the second electrode 9 sequentially stacking gradually with this.The first electrode 5 can comprise aluminium (Al) class reflector 5a and the transparency conducting layer 5b stacking gradually on substrate.Aluminium (Al) class reflector 5a can comprise for example the first element and nickel (Ni).
Substrate 1 can be any suitable substrate for organic light emitting apparatus, can be for example to have excellent mechanical strength, thermal stability, transparency, surface smoothness, be easy to process and glass substrate or the transparent plastic substrate of fire resistance characteristic.
The first element in aluminium (Al) class reflector 5a can comprise at least one in for example lanthanum (La), cerium (Ce), praseodymium (Pr), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb) and lutetium (Lu).
Aluminium (Al) class reflector 5a can have high reflectance, can improve thus the luminous efficiency of OLED.In addition, aluminium (Al) class reflector 5a is because the characteristic of Al can have high thermal stability.Thus, aluminium (Al) is even if class reflector 5a also has excellent durability in being exposed to high temperature process process.In addition, aluminium (Al) class reflector 5a can have excellent adhesion characteristic to the organic layer being adjacent or inorganic layer.
Therefore, aluminium (Al) class reflector substantially can be not separated at negative electrode engaging zones with transparent ITO conductive layer.
Aluminium (Al) class reflector 5a and transparency conducting layer 5b can be in contact with one another.But substantially can there is not the undesirable electrochemical corrosion causing due to the electrical potential difference between aluminium (Al) class reflector 5a and transparency conducting layer 5b.
Electrochemical corrosion meeting, because the electrical potential difference between two kinds of different metals that are adjacent to each other occurs, causes thus current flowing and produces electricity.Due to the different work contents in interface, a kind of another kind that can be used as negative electrode and have a relatively low activity (high potential) in two kinds of different metals that are in contact with one another with high activity (compared with low potential) relatively can be used as anode.When two kinds of metal exposed are in corrosive solution, the two can be because the electrical potential difference between them is corroded.This is known as electrochemical corrosion.Have the negative electrode of greater activity can be than independent use time corrosion fast, and have more SA anode, corrosion is slowly can be than independent uses time.Along with this electrochemical corrosion is propagated along the interface of two electrode layers that formed by different metal, the contact resistance between two electrodes can increase suddenly.Therefore, contact resistance can distribute very astatically.Thus, when the OLED operation that comprises these two electrode layers, the pixel of OLED can the inconsistent color of display brightness.Due to this inhomogeneous brightness, picture quality can obviously decline.Thereby electrochemical corrosion can become deterioration factor in OLED.
Yet because aluminium (Al) class reflector 5a comprises below by the first element describing in detail, this electrochemical corrosion can not occur substantially between aluminium (Al) class reflector 5a and transparency conducting layer 5b.Therefore, according to the OLED of present embodiment, can there is excellent quality.
Aluminium (Al) class reflector 5a can comprise for example nickel (Ni).Therefore, aluminium (Al) class reflector 5a can comprise that x is approximately 2.5 to approximately 3.5 Al
xni phase.
Fig. 2 A shows transmission electron microscope (TEM) image of the cross section in the Al class reflector (layer A) being formed on titanium (Ti) layer (layer B), and wherein Al class reflector comprises the nickel (Ni) of 2wt% and the lanthanum (La) of 0.35wt%.Fig. 2 B shows scanning transmission electron microscope (STEM)-angle of elevation ring-type darkfield image of the aluminium shown in Fig. 2 A (Al) based reflection film.Fig. 2 C shows the result of the sxemiquantitative X-ray energy dispersion spectrum of the irregular grown crystal (in the first and second measurement point) about appearing dimmed in Fig. 2 A.As shown in Figure 2 C, the irregular grown crystal in Fig. 2 A comprises Al and Ni with the ratio of Al (K): Ni (K)=73:27 (atom %).Therefore, aluminium (Al) class reflector 5a probably comprises that x is approximately 3 Al
xni phase.
X is approximately 2.5 to approximately 3.5 Al
xni can contact transparency conducting layer 5b mutually.
In addition, rich Ni oxide skin(coating) can further be arranged in aluminium (Al) class reflector 5a on the surface of transparency conducting layer 5b.
Fig. 3 shows the cross section TEM image of the structure that comprises the Al class reflector (region C) that is formed on successively on TFT substrate and transparent ITO conductive layer (region D), and wherein Al class reflector comprises the nickel (Ni) of 2wt% and the lanthanum (La) of 0.35wt%.In Fig. 3, the range of linearity being represented by " E " between Al class reflector and transparent ITO conductive layer is the rich Ni oxide skin(coating) to about 8nm corresponding to the about 7nm of thickness.
Because above-mentioned x is approximately 2.5 to approximately 3.5 Al
xni phase and/or rich Ni oxide skin(coating) can be realized ohmic contact between Al class reflector 5a and transparency conducting layer 5b.
Ni can about 0.6wt% to about 5wt%, for example about 1wt% is included in Al class reflector 5a to the amount of about 4wt%.In Al class reflector 5a, keep the amount of Ni can contribute to guarantee to make the contact resistance between Al class reflector 5a and transparency conducting layer 5b stable to about 5wt% at about 0.6wt%, and substantially can not reduce reflectivity and the chemical-resistant of Al class reflector 5a.In a kind of enforcement, the amount of Ni in Al class reflector 5a can be about 2wt%.Yet the amount of Ni in Al class reflector 5a is not limited to this tittle.
Except having the Ni of above-mentioned functions, Al class reflector 5a also can comprise the first element.The first element can comprise at least one in for example lanthanum (La), cerium (Ce), praseodymium (Pr), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb) and lutetium (Lu).
Because Al class reflector 5a can comprise above listed the first element, Al class reflector 5a can have excellent thermal stability, and can suppress electrochemical corrosion.For example, the first element can comprise lanthanum (La), but is not limited to this.
The content of the first element can be about 0.1wt% to about 3wt%, and for example about 0.1wt% is to about 1wt%.To be about 0.1wt% can contribute to guarantee that the thermal stability of Al in Al class reflector 5a and the reflectivity of Al class reflector 5a all can not reduce to about 3wt% to the amount that keeps the first element.The amount of the first element is not limited to above scope.For example, the content of the first element can be about 0.3wt% to about 0.35wt%, but is not limited to this.
Al class reflector 5a can have about 50nm or larger thickness, and for example about 100nm is to about 500nm.The thickness that keeps Al class reflector 5a is for about 50nm or can contribute to more greatly to guarantee substantially to prevent that the light because producing in organic layer 7 from causing the decline in luminous efficiency through Al class reflector 5a.
Transparency conducting layer 5b can be formed by for example transparent conductive metal oxide.The example of transparent conductive metal oxide comprises ITO and tin oxide (SnO
2), but be not limited to this.In a kind of enforcement, transparency conducting layer 5b can be formed by ITO.
Transparency conducting layer 5b can have about 5nm to about 100nm, and for example about 7nm is to the thickness of about 80nm.To be about 5nm can contribute to guarantee to make the reduction of the reflectivity of Al class reflector 5a to minimize to about 100nm to the thickness that keeps transparency conducting layer 5b, and OLED has excellent efficiency.
The ground floor 6 that comprises the compound of cyano-containing can be formed on transparency conducting layer 5b.The compound of the cyano-containing comprising due to ground floor 6 has two class single electron reduction-states, so the compound of cyano-containing can have the π-electron system (can confirm by for example cyclic voltammetry) of the expansion that can form stabilized radical.Thus, ground floor 6 can reduce the hole injection barrier from the first electrode 5 to organic layer 7.Therefore the OLED that, comprises the ground floor 6 with cyano-containing compound can have excellent driving voltage characteristic and excellent power efficiency characteristic was.
The compound of the cyano-containing that ground floor 6 comprises can comprise a kind of in the compound of following general formula 1 to 20 expression.
In general formula 1 to 20, X
1to X
4a kind of expression in general formula 30A to 30D independently of one another; Y
1to Y
8can be N or C (R independently of one another
103); Z
1to Z
4can be C or N independently of one another; A
1and A
2can be independently of one another-O-,-S-,-N (R
104) or C (R
105) (R
106)-; Q
101and Q
102can be C independently of one another
2~C
10alkylidene, C
2~C
10alkenylene, or by halogen atom, cyano group, hydroxyl, C
1~C
10alkyl or C
1~C
10the C that replaces of alkoxyl
2~C
10alkylidene or C
2~C
10alkenylene; T
1and T
2can be C independently of one another
5~C
30aromatic ring system, C
2~C
30hetero-aromatic ring system, or by halogen atom, cyano group, hydroxyl, C
1~C
10alkyl and C
1~C
10alkoxyl in the C of at least one replacement
5~C
30aromatic ring system or C
2~C
30hetero-aromatic ring system; P can be 1 to 10 integer; Q can be 0 to 10 integer; R
101to R
106can be hydrogen atom independently of one another, halogen atom, cyano group, hydroxyl, C
1~C
10alkyl, C
1~C
10alkoxyl, by halogen atom, cyano group, hydroxyl, C
5~C
14aryl and C
2~C
14heteroaryl in the C of at least one replacement
1~C
10alkyl, by halogen atom, cyano group, hydroxyl, C
5~C
14aryl and C
2~C
14heteroaryl in the C of at least one replacement
1~C
10alkoxyl,
or-N (R
107) (R
108); R
107and R
108be hydrogen atom, C independently of one another
1~C
10alkyl, phenyl or xenyl; And L
101can be C
5~C
14arlydene, C
5~C
14heteroarylidene, and by halogen atom, cyano group, hydroxyl, C
1~C
10alkyl or C
1~C
10alkoxyl in the C of at least one replacement
5~C
14arlydene or C
5~C
14heteroarylidene:
For example, in general formula 1 to 20, X
1to X
4can be represented by general formula 30A or 30D.
For example, in general formula 1 to 20, R
103can be hydrogen atom, halogen atom, cyano group, C
1~C
10alkyl, C
1~C
10alkoxyl, by the C of at least one replacement in halogen atom, cyano group, phenyl, naphthyl, anthryl, pyridine radicals, thiophenyl and benzo thiophenyl
1~C
10alkyl or C
1~C
10alkoxyl; Or-N (R
107) (R
108), R wherein
107and R
108can be hydrogen atom, C independently of one another
1~C
10alkyl, phenyl or xenyl.
For example, R
103can be the methyl of hydrogen atom ,-F, cyano group, methyl, ethyl, propyl group, vinyl, methoxyl group, ethyoxyl, propoxyl group, phenyl replacement, the propyl group that phenyl replaces, or-N (xenyl) (xenyl), but be not limited to this.
In general formula 1 and 2, R
101and R
102can be independently of one another cyano group,
but be not limited to this.
The compound of general formula 1 can be following compound 20, but is not limited to this.
In general formula 1 to 20, A
1and A
2can be-S-, but be not limited to this.
In general formula 20, Q
101and Q
102can be ethylidene independently of one another, propylidene, ethenylidene, allylidene; By the ethylidene of at least one replacement in halogen atom, cyano group, hydroxyl, by the propylidene of at least one replacement in halogen atom, cyano group, hydroxyl, by the ethenylidene of at least one replacement in halogen atom, cyano group, hydroxyl, or by the allylidene of at least one replacement in halogen atom, cyano group, hydroxyl.For example, Q
101and Q
102can be ethylidene independently of one another, ethenylidene, the ethylidene of at least one replacement in use-F and cyano group; Or with the ethenylidene of at least one replacement in-F and cyano group, but be not limited to this.
In general formula 1 to 20, T
1and T
2in each can be C
5~C
30aromatic ring system; C
2~C
30hetero-aromatic ring system; Or by halogen atom, cyano group, hydroxyl, C
1~C
10alkyl or C
1~C
10the C of at least one replacement of alkoxyl
5~C
30aromatic ring system or C
2~C
30hetero-aromatic ring system, wherein each in these systems comprises Z
1and Z
2, or Z
3and Z
4as structure division.As shown in general formula 1 to 20, T
1and T
2in each can on one or more positions of the skeleton of the compound by general formula 1 to 20 expression, be condensed.
C
5~C
30aromatic ring system refer to the carbocyclic aromatic system that comprises at least one aromatic ring and 5 to 30 carbon atoms.In this, using term " system " is in order to represent C
5~C
30aromatic ring system also comprise multiring structure.When aromatic ring system comprises 2 or more ring, these 2 or more ring can condense together or by singly-bound and be connected to each other.In a kind of enforcement, aromatic ring system can be C
6~C
30aromatic ring system.C
2~C
30hetero-aromatic ring system refer to the heterocyclic aromatic system that comprises at least one aromatic ring and 2 to 30 carbon atoms.For example, C
2~C
30hetero-aromatic ring system can comprise at least one hetero-atom selecting in the group that free nitrogen (N), oxygen (O), phosphorus (P) and sulphur (S) forms, and other ring atoms are carbon (C).If C
2~C
30hetero-aromatic ring system except hetero-aromatic ring, also further comprise at least one of aromatic ring and hetero-aromatic ring, these rings can condense mutually.C
5~C
30the example of aromatic ring system comprise benzene, pentalene, indenes, naphthalene, azulenes, heptalene, indacene (indacene), acenaphthene, fluorenes, non-that alkene (phenalene), phenanthrene, anthracene, fluoranthene, benzophenanthrene, pyrene, benzacridine, aphthacene, Pi, perylene, pentacene and hexacene, but be not limited to this.
For example, C
2~C
30hetero-aromatic ring system can be pyrroles, pyrazoles, imidazoles, imidazoline, pyridine, pyrazine, pyrimidine, indoles, purine, quinoline, phthalazines, indolizine, naphthyridines, quinazoline, cinnolines, indazole, carbazole, azophenlyene, phenanthridines, pyrans, benzopyran, benzofuran, thiophene, benzothiophene, isothiazole, isoxazole, thiadiazole Huo oxadiazole, but be not limited to this.
For example, in general formula 1 to 20, T
1and T
2can be benzene independently of one another, naphthalene, anthracene, thiophene, thiadiazole , oxadiazole, or by halogen atom, cyano group, C
1~C
10alkyl and C
1~C
10alkoxyl in benzene, naphthalene, anthracene, thiophene, the thiadiazole Huo oxadiazole of at least one replacement, but be not limited to this.
In general formula 1 to 20, p can be 1, but is not limited to this.In general formula 1 to 20, q can be 0,1 or 2, but is not limited to this.For example, in general formula 3, q is 0, the compound being represented by general formula 3 compound that following general formula 3A represents of can serving as reasons.
In general formula 2, L
101can be C
5~C
14arlydene, C
4~C
14or C
5~C
14heteroarylidene, or by halogen atom, cyano group, hydroxyl, C
1~C
10alkyl and C
1~C
10alkoxyl in the C of at least one replacement
5~C
14arlydene or C
4~C
14or C
5~C
14heteroarylidene.For example, L
101can be sub-thiophenyl, the sub-thiophenyl of benzo, by halogen atom, cyano group and C
1~C
10alkyl in the sub-thiophenyl of at least one replacement, or by halogen atom, cyano group and C
1~C
10alkyl in the sub-thiophenyl of benzo of at least one replacement, but be not limited to this.
According to an execution mode, a kind of expression that the compound of the cyano-containing that the ground floor 6 of OLED10 comprises can be in following general formula 1A to 20B:
In general formula 1A to 20B, R
103and R
109can be hydrogen atom ,-F, cyano group, methyl, ethyl, propyl group, methoxyl group, ethyoxyl or propoxyl group independently of one another.
According to another execution mode, the compound of the cyano-containing that the ground floor 6 of OLED10 comprises can be by a kind of expression of general formula 20A or 20B.In general formula 20A and 20B, R
103and R
109can be-F.
Except the compound of above-mentioned cyano-containing, ground floor 6 can further comprise hole transport compound.The compound of cyano-containing can form electric charge transmission complex compound together with hole transport compound, causes that thus free carrier concentration increases.Therefore, use hole transport compound can be conducive to reduce the interface resistance between the first electrode 5 and organic layer 7.
Hole transport compound can be any suitable hole mobile material.
In one embodiment, the hole transport compound compounds that following general formula 41 or 42 represents of can serving as reasons:
In general formula 41 and 42, R
10can be by-(Ar
1)
n-Ar
2represent; R
16can be by-(Ar
11)
m-Ar
12represent; Ar
1, Ar
11, L
1and L
11can be independently of one another for replacing or unsubstituted C
1~C
30alkylidene, replacement or unsubstituted C
2~C
30alkenylene, replacement or unsubstituted C
5~C
30arlydene, replacement or unsubstituted C
4~C
30heteroarylidene or by-N (Q
1the group of)-represent; N, m, a and b can be 0 to 10 integer independently of one another; R
1to R
3, R
11to R
15, R
17, R
18, R
21to R
29, Ar
2, Ar
12and Q
1can be hydrogen atom, halogen atom, hydroxyl, cyano group, replacement or unsubstituted C independently of one another
1~C
30alkyl, replacement or unsubstituted C
2~C
30thiazolinyl, replacement or unsubstituted C
2~C
30alkynyl, replacement or unsubstituted C
1~C
30alkoxyl, replacement or unsubstituted C
1~C
30alkylthio group, replacement or unsubstituted C
5~C
30aryl, replacement or unsubstituted C
4~C
30heteroaryl or by-N (Q
2) (Q
3) group that represents; And Q
2and Q
3can be hydrogen atom, halogen atom, hydroxyl, cyano group, replacement or unsubstituted C independently of one another
1~C
30alkyl, replacement or unsubstituted C
2~C
30thiazolinyl, replacement or unsubstituted C
2~C
30alkynyl, replacement or unsubstituted C
1~C
30alkoxyl, replacement or unsubstituted C
1~C
30alkylthio group, replacement or unsubstituted C
5~C
30aryl or replacement or unsubstituted C
4~C
30heteroaryl, wherein ,-(Ar
1)
n-in n Ar
1base can be same to each other or different to each other ,-(Ar
11)
m-in m Ar
11base can be same to each other or different to each other ,-(L
1)
a-in a L
1base can be same to each other or different to each other, and-(L
11)
b-in b L
11base can be same to each other or different to each other.
For R
10general formula-(Ar
1)
n-Ar
2in Ar
1with for R
16general formula-(Ar
11)
m-Ar
12in Ar
11example can comprise and replacing or unsubstituted C
1~C
10alkylidene, replacement or unsubstituted C
2~C
10alkenylene, replace or unsubstituted phenylene, replace or unsubstituted sub-pentalene base, replace or unsubstituted sub indenyl, replace or unsubstituted naphthylene, replace or unsubstituted sub-azulenes alkyl, replace or unsubstituted sub-heptalene base, replace or unsubstituted sub-indacene base, replace or unsubstituted sub-acenaphthenyl, replace or unsubstituted fluorenylidene, replace or that thiazolinyl of unsubstituted Asia and Africa, replace or unsubstituted phenanthrylene, replace or unsubstituted anthrylene, replace or unsubstituted sub-fluoranthene base, replace or unsubstituted sub-benzo phenanthryl, replace or unsubstituted sub-pyrenyl, replace or unsubstituted sub-benzacridine base, replace or unsubstituted sub-aphthacene base, replace or unsubstituted Ya Pi base, replace or unsubstituted Ya perylene base, replace or unsubstituted sub-pentacene base, replace or unsubstituted sub-hexacene base, replace or unsubstituted sub-pyrrole radicals, replace or unsubstituted sub-pyrazolyl, replace or unsubstituted sub-imidazole radicals, replace or unsubstituted sub-imidazolinyl, replace or unsubstituted sub-imidazopyridyl, replace or unsubstituted sub-imidazopyrimidine base, replace or unsubstituted sub-pyridine radicals, replace or unsubstituted sub-pyrazinyl, replace or unsubstituted sub-pyrimidine radicals, replace or unsubstituted sub-indyl, replace or unsubstituted sub-purine radicals, replace or unsubstituted sub-quinolyl, replace or unsubstituted sub-phthalazinyl, replace or unsubstituted sub-indolizine base, replace or unsubstituted sub-naphthyridines base, replace or unsubstituted sub-quinazolyl, replace or unsubstituted sub-cinnolines base, replace or unsubstituted sub-indazolyl, replace or unsubstituted sub-carbazyl, replace or unsubstituted sub-phenazinyl, replace or unsubstituted sub-phenanthridinyl, replace or unsubstituted sub-pyranose, replace or unsubstituted sub-benzopyran base, replace or unsubstituted sub-benzofuranyl, replace or unsubstituted sub-thienyl, replace or unsubstituted sub-benzothienyl, replace or unsubstituted sub-isothiazolyl, replace or unsubstituted sub-benzimidazolyl, replace or unsubstituted Ya isoxazolyl, replace or unsubstituted sub-triazine radical and by-N (Q
1the group of)-represent, but be not limited to this.At this, Q
1optional free hydrogen atom, halogen atom, hydroxyl, cyano group, replacement or unsubstituted C
1~C
10alkyl, replacement or unsubstituted C
2~C
10thiazolinyl, replacement or unsubstituted C
2~C
10alkynyl, replacement or unsubstituted C
1~C
10alkoxyl, replacement or unsubstituted C
1~C
10alkylthio group, replacement or unsubstituted C
5~C
14aryl, replacement or unsubstituted C
4~C
14heteroaryl and-N (Q
2) (Q
3) in the group that forms, but be not limited to this.
For example, Ar
1and Ar
11can be C independently of one another
1~C
10alkylidene, phenylene, naphthylene, anthrylene, fluorenylidene, sub-carbazyl, sub-pyrazolyl, sub-pyridine radicals, sub-triazine radical ,-N (Q
1)-; Or by halogen atom, cyano group, hydroxyl, C
1~C
10alkyl, C
1~C
10alkoxyl, phenyl, naphthyl and anthryl in the C of at least one replacement
1~C
10alkylidene, phenylene, naphthylene, anthrylene, fluorenylidene, sub-carbazyl, sub-pyrazolyl, sub-pyridine radicals or sub-triazine radical.At this, Q
1can be hydrogen atom, C
1~C
10alkyl, C
1~C
10alkoxyl, phenyl, naphthyl, carbazyl, fluorenyl, pyrenyl, by halogen atom, cyano group, hydroxyl, C
1~C
10alkyl, C
1~C
10alkoxyl, phenyl, naphthyl and anthryl in the C of at least one replacement
1~C
10alkyl, C
1~C
10alkoxyl, phenyl, naphthyl, carbazyl or pyrenyl; Or-N (Q
2) (Q
3).At this, Q
2and Q
3in each can be methyl, phenyl, naphthyl or anthryl.
At general formula-(Ar
1)
n-Ar
2in Ar
1and general formula-(Ar
11)
m-Ar
12in Ar
11can limit as above-mentioned Q
1the same.
At general formula-(Ar
1)
n-Ar
2in n and general formula-(Ar
11)
m-Ar
12in m can be 0 to 10 integer independently of one another.For example, n and m can be 0,1,2,3,4 or 5 independently of one another, but are not limited to this.
General formula-(Ar
1)
n-Ar
2in n Ar
1base can be same to each other or different to each other.For example, when n is 2, general formula-(Ar
1)
n-Ar
2in two Ar
1base can be phenylene simultaneously, or a can be-N (Q in two
1)-, and another can be phenylene.Also be applicable to-(Ar of this explanation
11)
m-Ar
12.
R in general formula 41 and 42
1to R
3, R
11to R
15, R
17, R
18and R
21to R
29can limit as above-mentioned Q
1the same.
For example, R
13can be phenyl, naphthyl or anthryl, but be not limited to this.
For example, R
28and R
29can be hydrogen atom, methyl, ethyl, methoxyl group, ethyoxyl, phenyl, naphthyl or anthryl independently of one another, but be not limited to this.
L in general formula 41 and 42
1and L
2can limit as above-mentioned Ar
1and Ar
11the same.
For example, L
1and L
2can be phenylene, C independently of one another
1~C
10alkyl phenylene, fluoro phenylene, sub-carbazyl, sub-triazine radical, C
1~C
10the sub-triazine radical of the sub-triazine radical of alkyl, phenyl, C
1~C
10alkylidene or the sub-carbazyl of phenyl, but be not limited to this.
In general formula 41 and 42, a and b can be 0 to 10 integer independently of one another.For example, a and b can be 0,1,2 or 3 independently of one another, but are not limited to this.
For example,, in general formula 42, for R
10general formula-(Ar
1)
n-Ar
2in Ar
1with for R
16general formula-(Ar
11)
m-Ar
12in Ar
11can be phenylene independently of one another; Sub-carbazyl; Fluorenylidene; Methyl fluorenylidene; Sub-pyrazolyl; The sub-pyrazolyl of phenyl;-N (Q
1)-, be Q wherein
1for hydrogen atom, phenyl, fluorenyl, dimethyl fluorenyl, diphenyl fluorenyl, carbazyl or phenyl carbazole base; Diphenyl fluorenylidene; Sub-triazine radical; The sub-triazine radical of methyl; The sub-triazine radical of phenyl; Tetrafluoro phenylene; Ethylidene; Or methylphenylene; Wherein n and m can be 0,1,2,3,4,5 or 6 independently of one another, and Ar
2and Ar
12can be hydrogen atom, cyano group, fluorine-based, phenyl, cyano-phenyl, naphthyl, anthryl, methyl, pyridine radicals, carbazyl, phenyl carbazole base, fluorenyl, dimethyl fluorenyl or diphenyl fluorenyl independently of one another.In general formula 42, R
11, R
12, R
14, R
15, R
17, R
18, R
21to R
27can be hydrogen atom; R
13can be phenyl, naphthyl or anthryl; R
28and R
29can be hydrogen atom, methyl, ethyl, methoxyl group, ethyoxyl, phenyl, naphthyl or anthryl independently of one another; L
11can be phenylene; And b can be 0 or 1.
For example, in general formula 42, R
13a kind of expression that can be in general formula 101A to 101D.
For example, in general formula 42, L
11can be phenylene, and b can be 1.
For example, in general formula 42, R
10a kind of expression that can be in general formula 102A to 102G.
For example, in general formula 42, R
28and R
29can be methyl or phenyl independently of one another.
For example, in general formula 42, R
11, R
12, R
14to R
18and R
21to R
27can be hydrogen atom.
For example, in general formula 41, R
1, R
2, R
3can be independently C separately
1-C
10alkyl; C
1-C
10alkoxyl; Phenyl; Naphthyl; Carbazyl; Fluorenyl; Pyrenyl; Anthryl; Pyrazolyl; Pyridine radicals; By halogen atom, cyano group, hydroxyl, C
1-C
10alkyl, C
1-C
10alkoxyl, phenyl, cyano-phenyl, hexichol amido, naphthyl, carbazyl, fluorenyl, C
1-C
10alkyl fluorenyl, two (C
1-C
10alkyl) C of at least one replacement in fluorenyl, phenyl fluorenyl, two (phenyl) fluorenyl and anthryl
1-C
10alkyl, C
1-C
10alkoxyl, phenyl, naphthyl, carbazyl, fluorenyl, pyrenyl, anthryl, pyrazolyl or pyridine radicals; Or-N (Q
2) (Q
3).At this, Q
2and Q
3in each can be C independently of one another
1-C
10alkyl; C
1-C
10alkoxyl; Phenyl; Naphthyl; Carbazyl; Fluorenyl; Pyrenyl; Anthryl; Pyrazolyl; Pyridine radicals; Or with halogen atom, cyano group, hydroxyl, C
1-C
10alkyl, C
1-C
10alkoxyl, phenyl, cyano-phenyl, hexichol amido, naphthyl, carbazyl, fluorenyl, C
1-C
10alkyl fluorenyl, two (C
1-C
10alkyl) C of at least one replacement of fluorenyl, phenyl fluorenyl, two (phenyl) fluorenyl and anthryl
1-C
10alkyl, C
1-C
10alkoxyl, phenyl, naphthyl, carbazyl, fluorenyl, pyrenyl, anthryl, pyrazolyl or pyridine radicals.
For example, in general formula 41, R
1, R
2, R
3can be independently a kind of with in following formula 201 to 226 separately.
In a kind of enforcement, hole mobile material compound any of following compound 1 to 38 expression of can serving as reasons, but be not limited to this.
Except the compound of cyano-containing, when ground floor 6 also further comprises above-mentioned hole transport compound, described ground floor based on 100 weight portions, the amount of the compound of the cyano-containing that ground floor 6 comprises can be approximately 0.1 weight portion to approximately 20 weight portions, approximately 0.5 weight portion to approximately 10 weight portions or approximately 0.5 to approximately 5 weight portion.The amount that keeps the compound of cyano-containing is that approximately 0.1 weight portion to approximately 20 weight portions can contribute to guarantee to obtain satisfied driving voltage reduction and power efficiency increase effect.
The thickness of ground floor 6 can be approximately
extremely approximately
approximately
extremely approximately
or approximately
extremely approximately
the thickness that keeps ground floor 6 is approximately
extremely approximately
can contribute to guarantee to obtain satisfied driving voltage reduction and power efficiency and increase effect.
Organic layer 7 can be arranged on the first electrode 5.The term using in whole specification " organic layer " refers to any insert layer (although above-mentioned ground floor 6 is from wherein getting rid of) between the first electrode 5 and the second electrode 9.Organic layer 7 can not be formed by pure organic materials, and can comprise for example metal complex.
Organic layer 7 can comprise luminescent layer (EML).
Distance between ground floor 6 and EML can be approximately
or larger, or approximately
or larger or approximately
extremely approximately
keep distance between ground floor 6 and EML for approximately
or the compound that can contribute to more greatly to guarantee the cyano-containing that the exciton that comprises in EML can not comprised by ground floor 6 substantially extinguishes, thereby can obtain having the OLED of excellent quality.
Except EML, organic layer 7 can further comprise at least one in hole injection layer (HIL), hole transmission layer (HTL), hole blocking layer (HBL), electron transfer layer (ETL) and electron injecting layer (EIL).
For example, at least one of HIL and HTL can further be inserted between ground floor 6 and EML.For example, HTL can further be inserted between ground floor 6 and EML.
HIL can be formed on ground floor 6 by such as vacuum deposition method, spin-coating method, flow coat method, LB sedimentation etc.
When HIL forms with vacuum deposition method, sedimentary condition can change according to structure and the hot property of the HIL that is used to form the compound of HIL and will forms.But conventionally, for the condition of vacuum deposition method, can comprise the depositing temperature, approximately 10 of approximately 100 to approximately 500 ℃
-18to approximately 10
-3the vacuum pressure of holder and approximately 0.01 is to approximately
deposition rate.
When HIL forms with spin-coating method, coating condition can change according to structure and the hot property of the HIL that is used to form the compound of HIL and will forms.But conventionally, for the condition of spin-coating method, can comprise approximately 2000 heat treatment temperatures to the coating speed of about 5000rpm and approximately 80 to approximately 200 ℃, wherein after coating, implement heat treatment with except desolventizing.
HIL can be formed by any appropriate materials that is generally used for forming HIL.The examples of materials that can be used for forming HIL can comprise the phthalocyanine compound, 4 such as copper phthalocyanine, 4', 4 " tri-(3-tolyl phenyl amino) triphenylamine (m-MTDATA), N; N '-bis-(1-naphthyl)-N; N '-diphenylbenzidine (NPB), TDATA, 2T-NATA, polyaniline/DBSA (Pani/DBSA), poly-(3; 4-ethylenedioxy thiophene)/poly-(4-styrene sulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA) and polyaniline/gather (4-styrene sulfonate) (PANI/PSS), but be not limited to this.
HIL can have approximately
extremely approximately
thickness, for example approximately
extremely approximately
thickness.The thickness that keeps HIL is for approximately
extremely approximately
can contribute to guarantee that HIL has excellent electronic injection ability and substantially do not increase driving voltage.
Then, HIL can be formed on HIL or ground floor 6 by using such as vacuum deposition method, spin-coating method, flow coat method, Langmuir-Blodgett (LB) sedimentation etc.When HIL forms with vacuum deposition method or spin-coating method, although can change according to the material that is used to form HTL for the condition that deposits or be coated with, can be similar in appearance to the condition that is used to form HIL for the condition that deposits and be coated with.
HTL can be formed by above-mentioned general formula 41 or 42 compounds that represent.
HTL can have approximately
extremely approximately
thickness, for example approximately
extremely approximately
thickness.The thickness that keeps HTL is for approximately
extremely approximately
can contribute to guarantee that HTL obtains excellent electron transport ability and substantially do not increase driving voltage.
Then, EML can be by being used such as vacuum deposition method, spin-coating method, flow coat method, LB sedimentation etc. to be formed on HTL.When EML forms with vacuum deposition method or spin-coating method, although can change according to the material that is used to form EML for the condition that deposits or be coated with, can be similar in appearance to the condition that is used to form HIL for the condition that deposits or be coated with.
EML can comprise conventional luminophor, or the combination of main body and dopant.The example of material of main part comprises Alq
3, 4,4'-N, N'-bis-carbazole biphenyl (CBP), TCTA, 1,3,5-tri-(N-phenyl benzimidazolyl-2 radicals-yl) benzene) (TPBI), E3, distyrene (DSA), the compound being represented by general formula 51, the compound being represented by general formula 52, the compound being represented by general formula 53 or the compound that represented by general formula 54, but be not limited to this.
In above general formula 51 to 54, Ar
51, A
52, Ar
53and Ar
54can limit as above-mentioned Ar
1the same.
In general formula 51 to 54, Ar
51, A
52, Ar
53and Ar
54can be the anthrylene that phenylene, naphthylene, anthrylene or phenyl replace independently of one another, but be not limited to this.
In general formula 51 to 54, R
201to R
209and R
51to R
56can limit as above-mentioned Ar
2the same.For example, R
201to R
209can be hydrogen.
In general formula 51 to 54, d, e, f and g can be 0 to 10 integer independently of one another.For example, d, e, f and g can be 0,1 or 2 independently of one another, but are not limited to this.
In general formula 51 to 54, R
51to R
56can be hydrogen atom, methyl, ethyl, propyl group, butyl, phenyl, naphthyl, anthryl, pyrenyl, carbazyl Huo – N (Q independently of one another
2) (Q
3), Q wherein
2and Q
3be methyl, phenyl, naphthyl or anthryl independently of one another.
In a kind of enforcement, the EML of organic layer 7 can comprise that a kind of compound by compound 51 to 58 expressions is as main body, but is not limited to this.
The example of red dopant can comprise PtOEP, Ir (piq)
3and Btp
2ir (acac), but be not limited to this.
The example of green dopant can comprise Ir (ppy)
3(ppy=phenylpyridine), Ir (ppy)
2and Ir (mpyp) (acac)
3, the compound by any one expression of general formula 51 to 54, the compound being represented by following general formula 71 and the compound being represented by general formula 72, but be not limited to this.
In general formula 71 and 72, Ar
71and Ar
72can limit as above-mentioned Ar
1the same.
In general formula 71 and 72, Ar
71and Ar
72can be the anthrylene that ethylidene, phenylene, naphthylene, anthrylene or phenyl replace independently of one another, but be not limited to this.
In general formula 71 and 72, R
211to R
216and R
71to R
76can limit as above-mentioned Ar
2the same.For example, R
211to R
216can be hydrogen.
In general formula 71 and 72, h and i can be 0 to 10 integer independently of one another.For example, h and i can be 0,1 or 2 independently of one another.
In general formula 71 and 72, R
71to R
76can be methyl, ethyl, vinyl, phenyl, tolyl, naphthyl, first naphthyl, anthryl, first anthryl, pyrenyl Huo – N (Q independently of one another
2) (Q
3), Q wherein
2and Q
3be methyl, phenyl, naphthyl or anthryl independently of one another.
In another kind is implemented, EML can comprise that a kind of compound by above compound 51 to 58,71 to 76 expressions of following compound is as green dopant, but is not limited to this.
The example of blue dopant can comprise F
2irpic, (F
2ppy)
2ir (tmd), Ir (dfppz)
3, tertiary fluorenes, 4, two (the 4-diphenyl amino styryl) biphenyl (DPAVBi), 2,5,8 of 4'-, 11-tetra-tert perylene (TBPe), by general formula 51,54,81 and 82 compounds that represent, but be not limited to this.
In general formula 81, L
21can be and replace or unsubstituted C
1~C
30alkylidene, replacement or unsubstituted C
2~C
30alkenylene, replacement or unsubstituted C
5~C
30arlydene or replacement or unsubstituted C
4~C
30heteroarylidene; C can be 1 to 20 integer;-(L
21)
c-in c L
21base can be same to each other or different to each other; R
31to R
34can be independently of one another for replacing or unsubstituted C
1~C
30alkyl, replacement or unsubstituted C
2~C
30thiazolinyl, replacement or unsubstituted C
2~C
30alkynyl, replacement or unsubstituted C
1~C
30alkoxyl, replacement or unsubstituted C
5~C
30aryl or replacement or unsubstituted C
4~C
30heteroaryl.
In general formula 81, L
21can limit as above-mentioned Ar
1the same (p-N (Q
1)-explanation except), and R
31to R
34can limit as above-mentioned Q
1the same (p-N (Q
2) (Q
3)-explanation except).
In an example of general formula 81, L
21can be ethenylidene, allylidene or phenylene.
In another example of general formula 81, c can be 1,2,3,4,5 or 6.
In another example of general formula 81, R
31to R
34can be hydrogen atom, methyl, ethyl, propyl group, butyl, methoxyl group, ethyoxyl, propoxyl group, butoxy, phenyl, naphthyl or anthryl independently of one another.
In general formula 81 ,-(L
21)
c-in c L
21base can be same to each other or different to each other.For example, when c is 2, two L
21base can be phenylene simultaneously, or in two one can be phenylene, and another can be ethenylidene.
In general formula 82, Ar
81and Ar
84can limit as above-mentioned Ar
1the same.
In general formula 82, Ar
31, Ar
32, Ar
33and Ar
34can be the anthrylene that phenylene, naphthylene, anthrylene or phenyl replace independently of one another, but be not limited to this.
In general formula 82, R
221to R
228and R
81to R
85can limit as above-mentioned Ar
2the same.For example, R
221to R
228can be hydrogen.
In general formula 82, j, k, l and m can be 0 to 10 integer independently of one another.For example, j, k, l and m can be 0,1 or 2 independently of one another.
In general formula 82, R
81to R
85can be hydrogen atom, methyl, ethyl, propyl group, butyl, phenyl, naphthyl, anthryl, pyrenyl, carbazyl Huo – N (Q independently of one another
2) (Q
3), Q wherein
2and Q
3be methyl, phenyl, naphthyl or anthryl independently of one another.
The compound of general formula 81 can be following compound 40, but is not limited to this.
The compound of general formula 82 can be represented by following compound 41 or 42, but be not limited to this.
In a kind of enforcement, EML can comprise any as blue dopant in compound 40 to 42,51 to 55,57 and 58, but is not limited to this.
When dopant is used as the material of EML together with main body, the main body based on 100 weight portions, the amount of dopant can be approximately 0.01 to the scope of approximately 15 weight portions.
EML can have approximately
extremely approximately
thickness, for example approximately
extremely approximately
thickness.The thickness that keeps EML is for approximately
extremely approximately
can contribute to guarantee that EML has excellent luminous power and substantially do not increase driving voltage.
When phosphorescent dopants is also used to form EML, HBL can be by using such as vacuum deposition method, spin-coating method, flow coat method, LB sedimentation etc. to be formed between HTL and EML, to prevent that triplet excitons or hole are diffused in ETL.When HBL forms with vacuum deposition method or spin-coating method, although can change according to the material that is used to form HBL for the condition that deposits and be coated with, can be similar in appearance to the condition that is used to form HIL for the condition that deposits or be coated with.Can use any appropriate materials that is generally used for forming HBL.The examples of materials that is used to form HBL can Bao Kuo oxadiazole derivative, triazole derivative and phenanthroline derivative, but is not limited to this.
HBL can have approximately
extremely approximately
thickness, for example approximately
extremely approximately
thickness.The thickness that keeps HBL is for approximately
extremely approximately
can contribute to guarantee that HBL has excellent hole barrier ability and substantially do not increase driving voltage.
ETL can be formed on HBL or EML by such as vacuum deposition method, spin-coating method, flow coat method, LB sedimentation etc.When ETL forms with vacuum deposition method or spin-coating method, although can change according to the compound that is used to form ETL for the condition that deposits or be coated with, can be similar in appearance to the condition that is used to form HIL for the condition that deposits and be coated with.The material that is used to form ETL can be any appropriate materials that can stably transmit by electron injection electrode (negative electrode) injected electrons.The examples of materials that is used to form ETL can comprise quinoline, for example three (oxine) aluminium (Alq
3), TAZ and Balq, but be not limited to this.
ETL can have approximately
extremely approximately
thickness, for example approximately
extremely approximately
thickness.The thickness that keeps ETL is for approximately
extremely approximately
can contribute to guarantee that ETL has gratifying electron transport ability and substantially do not increase driving voltage.
Then, EIL can be formed on ETL.EIL can be by any appropriate materials that electronics is easy to be injected by negative electrode is formed.
The examples of materials that is used to form EIL can comprise the known LiF in this area, NaCl, a CsF, Li
2o and BaO.Although can change according to the material that is used to form EIL for the condition that deposits or be coated with, being used to form the deposition of EIL and the condition of coating can be similar in appearance to the condition that is used to form HIL.
EIL can have approximately
extremely
thickness, for example approximately
extremely approximately
thickness.The thickness that keeps EIL is for approximately
extremely
can contribute to guarantee EIL to there is gratifying electronic injection ability and substantially not increase organic light emitting apparatus driving voltage.
Finally, on organic layer 7, form the second electrode 9.The second electrode 9 can be electron injection electrode negative electrode.The material that is used to form the second electrode 9 can comprise metal, alloy, conductive compound or their mixture for example with low work content.At this, the second electrode 9 can be formed by such as lithium (Li), magnesium (Mg), aluminium (Al), aluminium (Al)-lithium (Li), calcium (Ca), magnesium (Mg)-indium (In), magnesium (Mg)-Yin (Ag) etc., and can form film-type transmission electrode.In addition, transmission electrode can form to manufacture top light emitting-type light-emitting device by ITO or IZO.
For example, OLED can comprise the Al class reflector being formed by Al, Ni and La sequentially stacking gradually with this; The transparency conducting layer being formed by ITO; Comprise the ground floor (in this article, ground floor can further selectively comprise the hole transport compound being represented by general formula 42) by the cyano-containing compound of any one expression of general formula 1A to 20B; The HTL that comprises the compound being represented by general formula 42; The EML that comprises main body (by the compound of any one expression of general formula 51 to 54) and dopant (by the compound of any one expression of general formula 51 to 54,71 and 72); ETL; EIL; With the second electrode, and can launch and there is high-quality green glow.Green glow can send according to mechanism of fluorescence emission.The maximum emission peak wavelength of green glow can be about 490nm to about 560nm.
Or for example, OLED can comprise the Al class reflector being formed by Al, Ni and La sequentially stacking gradually with this; The transparency conducting layer being formed by ITO; Comprise by the ground floor of the cyano-containing compound of any one expression of general formula 20A and 20B (in this article, ground floor can further selectively comprise as hole transport compound by any one of compound 1 to 37 expression); Comprise any one HTL by compound 1 to 37 expression; The EML that comprises main body (by any one of chemical formula 51 to 58) and dopant (by any one of chemical formula 40 to 42,51 to 58); ETL; EIL; With the second electrode, and can launch and there is high-quality green glow.
Fig. 4 shows according to the schematic cross-section of the OLED30 of another execution mode.With reference to Fig. 4, according to the OLED30 of present embodiment, can comprise for example substrate 21, the first electrode 25, the ground floor 26 that comprises the compound of cyano-containing, organic layer 27 and the second electrode 29, wherein the first electrode 25 comprises the zinc oxide film 25c that is arranged sequentially in the Al class reflector 25a, the transparency conducting layer 25b that comprise nickel (Ni) and the first element on substrate 21 and contains the second element with this.Substrate 21, the first electrode 25, the ground floor 26 that comprises the compound of cyano-containing, organic layer 27, the second electrode 29, comprise that the Al class reflector 25a of Ni and the first element is identical with the above explanation with reference to Fig. 1 with transparency conducting layer 25b, thus can be with reference to above-mentioned explanation.
With reference to Fig. 4, compare with the OLED10 in Fig. 1, according in the OLED30 of present embodiment, the first electrode 25 can further comprise the zinc oxide film 25c containing the second element.Zinc oxide film 25c containing the second element can reduce hole injection barrier by improving the work content of the first electrode 25, thereby makes hole be easy to be injected into organic layer 27 from the first electrode 25.
In this, in the ground floor 26 of compound that comprises cyano-containing, the compound of cyano-containing can further strengthen the hole injection properties containing the zinc oxide film 25c of the second element.Therefore, can obtain thering is the OLED compared with low driving voltage and better power efficiency characteristic was.
Containing the second element in the zinc oxide film 25c of the second element, can comprise at least one in aluminium (Al), indium (In), gallium (Ga), germanium (Ge), gadolinium (Gd), zirconium (Zr), molybdenum (Mo) and nickel (Ni).For example, the second element can comprise aluminium (Al).The second element can be aluminium (Al), but is not limited to this.
The zinc oxide film 25c containing the second element based on 100 weight portions, the second element can be approximately 0.5 to approximately 10 weight portion at the content containing in the zinc oxide film 25c of the second element.Keep can contributing to guarantee that the zinc oxide film 25c containing the second element has the transmissivity that excellent cavity transmission ability does not substantially increase resistance or substantially do not reduce visible ray containing the amount of the second element in the zinc oxide film 25c of the second element for approximately 0.5 to approximately 10 weight portion.For example, the zinc oxide film 25c containing the second element based on 100 weight portions, the amount of the second element can be approximately 0.5 to approximately 5 weight portion, but is not limited to this.
Zinc oxide film 25c containing the second element can have approximately
extremely approximately
thickness, for example approximately
extremely approximately
thickness.Keep containing the thickness of the zinc oxide film 25c of the second element for approximately
extremely approximately
can contribute to guarantee to obtain excellent efficiency characteristic and substantially not increase driving voltage.
For example, OLED can comprise the Al class reflector being formed by Al, Ni and La sequentially stacking gradually with this; The transparency conducting layer being formed by ITO; Zinc oxide film containing Al; Comprise the ground floor (ground floor can further selectively comprise the hole transport compound being represented by general formula 42) by the compound of the cyano-containing of any one expression of general formula 1A to 20B herein; The HTL that comprises the compound being represented by general formula 42; The EML that comprises main body (by the compound of any one expression of general formula 51 to 54) and dopant (by the compound of any one expression of general formula 51 to 54 and 72); ETL; EIL; With the second electrode, and can launch and there is high-quality green glow.Green glow can send according to mechanism of fluorescence emission.The maximum emission peak wavelength of green glow can be about 490nm to about 560nm.
Or for example, OLED can comprise the Al class reflector being formed by Al, Ni and La sequentially stacking gradually with this; The transparency conducting layer being formed by ITO; Zinc oxide film containing Al; Comprise by the ground floor of the compound of the cyano-containing of any one expression of general formula 20A and 20B (herein, ground floor can further selectively comprise as hole transport compound by any one of compound 1 to 37 expression); Comprise any one HTL by compound 1 to 37 expression; The EML that comprises main body (any one of chemical formula 51 to 58) and dopant (any one of chemical formula 40 to 42,51 to 58); ETL; EIL; With the second electrode, and can launch and there is high-quality green glow.
In Fig. 1 and Fig. 4, illustrated according to the OLED10 of each execution mode and 30.Yet each execution mode is not limited to this.
For example, any one in OLED10 and 30 can further be included in the metal level between Al class reflector 5a (25a) and substrate 1 (21).Metal level is as stopping that the Al in Al class reflector 5a (25a) is diffused into the barrier layer in substrate 1 (21).Metal level can comprise at least one in molybdenum (Mo), tungsten (W), titanium (Ti), palladium (Pd), platinum (Pt) and gold (Au), but is not limited to this.For example, metal level can comprise titanium (Ti) layer.Metal level can have about 20nm to the thickness of about 200nm, and for example about 50nm is to the thickness of about 100nm.The thickness that keeps metal level is that about 20nm can contribute to guarantee effectively to prevent that aluminium (Al) from spreading to about 200nm.Yet the thickness of metal level is not limited to this.
OLED can further comprise at least one in HIL and HTL between the first electrode and ground floor.That is to say, for example OLED can comprise substrate, the first electrode, a HTL, ground floor, the 2nd HTL, EML, ETL, EIL and the second electrode sequentially stacking gradually with this.
Hereinafter, with reference to following examples, illustrate in greater detail one or more execution modes.Yet these embodiment are not intended to limit object and the scope of one or more execution modes.
Embodiment
Comparative example 1
By 15 Ω/cm
2(
) ito glass substrate (being buied by Corning Incorporated) be cut into the size of 50mm * 50mm * 0.7mm, with isopropyl alcohol, carry out Ultrasonic Cleaning 5 minutes, then with pure water, clean 5 minutes, and again clean 30 minutes with ultraviolet and ozone.The ito glass substrate making is used as to substrate and anode.Then, m-MTDATA vacuum moulding machine is formed on gained ito glass substrate
thick HIL then forms above compound 5 vacuum moulding machines on HIL
thick HTL.Above compound 58 using the above compound 56 of 97wt% as main body and 3wt% forms on HTL as dopant deposit
thick EML.On EML, vacuum moulding machine Alq3 forms
thick ETL.On ETL, vacuum moulding machine Liq forms
thick EIL, and vacuum moulding machine Mg and Al formation on EIL
thick negative electrode.Then, on negative electrode, vacuum moulding machine Alq3 forms
thick protective layer, thus the manufacture of OLED completed.
Embodiment 1
With the method identical with comparative example 1, manufacture OLED, difference is as substrate and anode, in order to this order, forms thereon successively
thick AlNiLa layer (in AlNiLa layer, the amount of nickel (Ni) is 2wt%, and the amount of lanthanum (La) is 0.3wt%),
thick ITO layer as transparency conducting layer and
the glass substrate of the thick zinc oxide film containing Al (content of Al is counted 2 weight portions with 100 weight portions containing the zinc oxide film of Al) replaces ito glass substrate; And comprising (the R wherein by general formula 20A containing forming on the zinc oxide film of Al
109for-F) compound representing and the ground floor of compound 14 replacement HIL, then form HTL, the amount of the compound wherein being represented by general formula 20A is counted 1 weight portion with 100 weight portion ground floors.
Embodiment 2
With the method identical with embodiment 1, manufacture OLED, difference is that the amount of the compound that represented by general formula 20A counts 3 weight portions with ground floor 100 weight portions.
Evaluate
With 238 high current sources (KEITHLEY), measure the driving voltage of the OLED manufacturing in comparative example 1 and embodiment 1 and 2.With PR650 spectral scan source determination unit (PhotoResearch), measure the power efficiency of the OLED manufacturing in comparative example 1 and embodiment 1 to 2.The results are shown in following table 1.
Table 1
? | Power efficiency (Im/W) | Driving voltage (V) |
Comparative example 1 | 14.5 | 5.1 |
Embodiment 1 | 18.6 | 4.5 |
Embodiment 2 | 16.3 | 4.6 |
With reference to table 1, the OLED that the OLED that can confirm embodiment 1 to 2 compares ratio 1 shows lower driving voltage and higher power efficiency.
As mentioned above, according to the OLED of execution mode, can there is excellent driving voltage characteristic and excellent power efficiency characteristic was.
At this, illustrative embodiments is disclosed, although and used concrete term, they only use and understand with common and illustrative approach, and are not used in the object of restriction.Therefore, those of ordinary skills should understand and can carry out the various changes in form and details and not deviate from the spirit and scope of the present invention of stating in appended claims.
Claims (32)
1. an organic light emitting apparatus, comprising:
Substrate;
The first electrode on described substrate;
The second electrode;
Organic layer between described the first electrode and the second electrode, described organic layer comprises luminescent layer; With
The ground floor that comprises the compound of cyano-containing, described ground floor between described the first electrode and described luminescent layer,
Wherein:
Described the first electrode comprises Al class reflector and the transparency conducting layer stacking gradually on described substrate, and described Al class reflector comprises the first element and nickel, and
Described the first element comprises at least one in lanthanum, cerium, praseodymium, promethium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium and lutetium;
Wherein in described Al class reflector, on the surface of described transparency conducting layer, further comprise rich nickel oxide layer, and
Wherein between the described Al class reflector of described the first electrode and described substrate, be provided with metal level, and described metal level comprises at least one in molybdenum (Mo), tungsten (W), titanium (Ti), palladium (Pd), platinum (Pt) and gold (Au).
2. organic light emitting apparatus according to claim 1, wherein said the first electrode further comprises the zinc oxide film containing the second element, described the second element comprises at least one in aluminium, indium, gallium, germanium, gadolinium, zirconium, molybdenum and nickel.
3. organic light emitting apparatus according to claim 2, wherein said Al class reflector, described transparency conducting layer and the described zinc oxide film that contains the second element sequentially stack gradually on described substrate with this.
4. organic light emitting apparatus according to claim 2, the described zinc oxide film that contains the second element based on 100 weight portions wherein, the content of described the second element is 0.5 to 10 weight portion.
5. organic light emitting apparatus according to claim 2, wherein said Al class reflector comprises La, Ni and Al.
6. organic light emitting apparatus according to claim 1, the compound of wherein said cyano-containing comprises any in the compound of general formula 1 to 20 expression:
In general formula 1 to 20,
X
1to X
4a kind of expression in general formula 30A to 30D independently of one another;
Y
1to Y
8be N or C (R independently of one another
103);
Z
1to Z
4be C or N independently of one another;
A
1and A
2be independently of one another-O-,-S-,-N (R
104) or C (R
105) (R
106)-;
Q
101and Q
102be C independently of one another
2~C
10alkylidene, C
2~C
10alkenylene, or by halogen atom, cyano group, hydroxyl, C
1~C
10alkyl or C
1~C
10alkoxyl in the C of at least one replacement
2~C
10alkylidene or C
2~C
10alkenylene;
T
1and T
2be C independently of one another
5~C
30aromatic ring system, C
2~C
30hetero-aromatic ring system, or by halogen atom, cyano group, hydroxyl, C
1~C
10alkyl or C
1~C
10alkoxyl in the C of at least one replacement
5~C
30aromatic ring system or C
2~C
30hetero-aromatic ring system;
P is 1 to 10 integer;
Q is 0 to 10 integer;
R
101to R
106be hydrogen atom independently of one another, halogen atom, cyano group, hydroxyl, C
1~C
10alkyl, C
1~C
10alkoxyl, by halogen atom, cyano group, hydroxyl, C
5~C
14aryl and C
2~C
14heteroaryl in the C of at least one replacement
1~C
10alkyl, by halogen atom, cyano group, hydroxyl, C
5~C
14aryl and C
2~C
14heteroaryl in the C of at least one replacement
1~C
10alkoxyl,
or-N (R
107) (R
108);
R
107and R
108be hydrogen atom, C independently of one another
1~C
10alkyl, phenyl or xenyl; And
L
101for C
5~C
14arlydene, C
5~C
14heteroarylidene, and by halogen atom, cyano group, hydroxyl, C
1~C
10alkyl and C
1~C
10alkoxyl in the C of at least one replacement
5~C
14arlydene or C
5~C
14heteroarylidene a kind of:
7. organic light emitting apparatus according to claim 6, wherein X
1to X
4by general formula 30A or 30D, represented independently of one another.
8. organic light emitting apparatus according to claim 6, wherein R
103for hydrogen atom, halogen atom, cyano group, C
1~C
10alkyl, C
1~C
10alkoxyl, by the C of at least one replacement in halogen atom, cyano group, phenyl, naphthyl, anthryl, pyridine radicals, thiophenyl and benzo thiophenyl
1~C
10alkyl or C
1~C
10alkoxyl, or-N (R
107) (R
108) a kind of, and
R wherein
107and R
108be hydrogen atom, C independently of one another
1~C
10alkyl, phenyl or xenyl.
9. organic light emitting apparatus according to claim 6, wherein R
101and R
102be independently of one another cyano group,
10. organic light emitting apparatus according to claim 6, wherein A
1and A
2be-S-.
11. organic light emitting apparatus according to claim 6, wherein Q
101and Q
102be ethylidene independently of one another, propylidene, ethenylidene, allylidene, by the ethylidene of at least one replacement in halogen atom, cyano group, hydroxyl, by the propylidene of at least one replacement in halogen atom, cyano group, hydroxyl, by the ethenylidene of at least one replacement in halogen atom, cyano group, hydroxyl, or by the allylidene of at least one replacement in halogen atom, cyano group, hydroxyl.
12. organic light emitting apparatus according to claim 6, wherein T
1and T
2be benzene independently of one another, naphthalene, anthracene, thiophene, thiadiazole , oxadiazole, or be by halogen atom, cyano group, C
1~C
10alkyl and C
1~C
10alkoxyl in benzene, naphthalene, anthracene, thiophene, the thiadiazole Huo oxadiazole of at least one replacement.
13. organic light emitting apparatus according to claim 6, wherein p is 1.
14. organic light emitting apparatus according to claim 6, wherein q is 0,1 or 2.
15. organic light emitting apparatus according to claim 6, wherein L
101for sub-thiophenyl, the sub-thiophenyl of benzo, by halogen atom, cyano group and C
1~C
10alkyl in the sub-thiophenyl of at least one replacement, with by halogen atom, cyano group and C
1~C
10alkyl in the sub-thiophenyl of benzo of at least one replacement in a kind of.
16. organic light emitting apparatus according to claim 6, the serve as reasons compound of any expression in following general formula 1A to 20B of the compound of wherein said cyano-containing:
R wherein
103and R
109be hydrogen atom ,-F, cyano group, methyl, ethyl, propyl group, vinyl, methoxyl group, ethyoxyl or propoxyl group independently of one another.
17. organic light emitting apparatus according to claim 1, wherein said ground floor further comprises hole transport compound.
18. organic light emitting apparatus according to claim 17, wherein said hole transport compound comprises by following general formula 41 or 42 compounds that represent:
R wherein
10by-(Ar
1)
n-Ar
2represent;
R
16by-(Ar
11)
m-Ar
12represent;
Ar
1, Ar
11, L
1and L
11independently of one another for replacing or unsubstituted C
1~C
30alkylidene, replacement or unsubstituted C
2~C
30alkenylene, replacement or unsubstituted C
5~C
30arlydene, replacement or unsubstituted C
4~C
30heteroarylidene or by-N (Q
1the group of)-represent;
N, m, a and b are 0 to 10 integer independently of one another.
R
1to R
3, R
11to R
15, R
17, R
18, R
21to R
29, Ar
2, Ar
12and Q
1be hydrogen atom, halogen atom, hydroxyl, cyano group, replacement or unsubstituted C independently of one another
1~C
30alkyl, replacement or unsubstituted C
2~C
30thiazolinyl, replacement or unsubstituted C
2~C
30alkynyl, replacement or unsubstituted C
1~C
30alkoxyl, replacement or unsubstituted C
1~C
30alkylthio group, replacement or unsubstituted C
5~C
30aryl, C
4~C
30heteroaryl or by-N (Q
2) (Q
3) group that represents; And
Q
2and Q
3be hydrogen atom, halogen atom, hydroxyl, cyano group, replacement or unsubstituted C independently of one another
1~C
30alkyl, replacement or unsubstituted C
2~C
30thiazolinyl, replacement or unsubstituted C
2~C
30alkynyl, replacement or unsubstituted C
1~C
30alkoxyl, replacement or unsubstituted C
1~C
30alkylthio group, replacement or unsubstituted C
5~C
30aryl or replacement or unsubstituted C
4~C
30heteroaryl,
Wherein-(Ar
1)
n-in n Ar
1base is same to each other or different to each other ,-(Ar
11)
m-in m Ar
11base is same to each other or different to each other ,-(L
1)
a-in a L
1base is same to each other or different to each other, and-(L
11)
b-in b L
11base is same to each other or different to each other.
19. organic light emitting apparatus according to claim 18, wherein Ar
1and Ar
11be C independently of one another
1~C
10alkylidene, phenylene, naphthylene, anthrylene, fluorenylidene, sub-carbazyl, sub-pyrazolyl, sub-pyridine radicals, sub-triazine radical ,-N (Q
1)-; Or by halogen atom, cyano group, hydroxyl, C
1~C
10alkyl, C
1~C
10alkoxyl, phenyl, naphthyl and anthryl in the C of at least one replacement
1~C
10alkylidene, phenylene, naphthylene, anthrylene, fluorenylidene, sub-carbazyl, sub-pyrazolyl, sub-pyridine radicals or sub-triazine radical,
Q wherein
1for hydrogen atom, C
1~C
10alkyl, C
1~C
10alkoxyl, phenyl, naphthyl, carbazyl, fluorenyl, pyrenyl, with selecting free halogen atom, cyano group, hydroxyl, C
1~C
10alkyl, C
1~C
10alkoxyl, phenyl, naphthyl and the C that replaces of at least one substituting group in the group that forms of anthryl
1~C
10alkyl, C
1~C
10alkoxyl, phenyl, naphthyl, carbazyl, fluorenyl or pyrenyl, or-N (Q
2) (Q
3) in a kind of.
20. organic light emitting apparatus according to claim 18, wherein Ar
2and Ar
12be hydrogen atom independently of one another, C
1~C
10alkyl, phenyl, naphthyl, carbazyl, fluorenyl, pyrenyl, by halogen atom, cyano group, hydroxyl, C
1~C
10alkyl, C
1~C
10alkoxyl, phenyl, naphthyl and anthryl in the C of at least one replacement
1~C
10alkyl, C
1~C
10alkoxyl, phenyl, naphthyl, carbazyl, fluorenyl or pyrenyl, or-N (Q
2) (Q
3), and
Q wherein
2and Q
3be hydrogen atom, methyl, ethyl, phenyl, tolyl, xenyl, naphthyl or first naphthyl independently of one another.
21. organic light emitting apparatus according to claim 18, wherein n and m are 0,1,2,3,4,5 or 6 independently of one another.
22. organic light emitting apparatus according to claim 16, the described ground floor based on 100 weight portions wherein, the content of the compound of cyano-containing described in described ground floor is 0.1 to 20 weight portion.
23. organic light emitting apparatus according to claim 1, wherein said ground floor has
extremely
thickness.
24. organic light emitting apparatus according to claim 1, the distance between wherein said ground floor and described luminescent layer is
or larger.
25. organic light emitting apparatus according to claim 1 wherein further comprise at least one in hole injection layer and hole transmission layer between described ground floor and described luminescent layer.
26. organic light emitting apparatus according to claim 1, wherein said Al class reflector comprises Al
xni phase, and x is 2.5 to 3.5.
27. organic light emitting apparatus according to claim 1, wherein said Al class reflector comprises Al
xni phase also contacts described transparency conducting layer, wherein said Al
xni mutually middle x is 2.5 to 3.5.
28. organic light emitting apparatus according to claim 27, wherein x is 3.
29. organic light emitting apparatus according to claim 1, the described Al class reflector based on 100 weight portions wherein, in described Al class reflector, the content of nickel is 0.6wt% to 5wt%.
30. organic light emitting apparatus according to claim 1, wherein said the first element comprises lanthanum.
31. organic light emitting apparatus according to claim 1, the described Al class reflector based on 100 weight portions wherein, described in described Al class reflector, the content of the first element is 0.1wt% to 3wt%.
32. organic light emitting apparatus according to claim 1, wherein, described transparency conducting layer comprises tin indium oxide or tin oxide.
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Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100964231B1 (en) * | 2008-08-29 | 2010-06-16 | 삼성모바일디스플레이주식회사 | Organic light emitting device and organic light emitting display apparatus |
KR101908384B1 (en) | 2011-06-17 | 2018-10-17 | 삼성디스플레이 주식회사 | Organic light-emitting diode and flat display device comprising the same |
WO2013008765A1 (en) * | 2011-07-08 | 2013-01-17 | Semiconductor Energy Laboratory Co., Ltd. | Light-emitting module, light-emitting device, and method for manufacturing the light-emitting module |
KR101927943B1 (en) | 2011-12-02 | 2018-12-12 | 삼성디스플레이 주식회사 | Organic light-emitting diode comprising multi-layered hole transporting layer, and flat display device including the same |
KR101927941B1 (en) | 2011-12-19 | 2018-12-12 | 삼성디스플레이 주식회사 | Organic light-emitting diode comprising multi-layered hole transporting layer, and flat display device including the same |
KR101952706B1 (en) * | 2012-07-24 | 2019-02-28 | 삼성디스플레이 주식회사 | Organic light-emitting device and organic light-emitting display apparatus including the same |
WO2014034795A1 (en) | 2012-08-31 | 2014-03-06 | 出光興産株式会社 | Aromatic amine derivative, and organic electroluminescent element using same |
DE102013105555A1 (en) * | 2013-05-29 | 2014-12-04 | Osram Opto Semiconductors Gmbh | Optoelectronic semiconductor component |
KR20150029530A (en) * | 2013-09-09 | 2015-03-18 | 삼성디스플레이 주식회사 | Organic light- emitting display apparatus |
US9257672B2 (en) * | 2013-09-09 | 2016-02-09 | Samsung Display Co., Ltd. | Organic light-emitting display apparatus |
CN103915571A (en) * | 2014-01-27 | 2014-07-09 | 上海天马有机发光显示技术有限公司 | AMOLED display panel and film manufacturing method and display device |
JP6157718B2 (en) | 2014-02-28 | 2017-07-05 | 出光興産株式会社 | COMPOUND, MATERIAL FOR ORGANIC ELECTROLUMINESCENT ELEMENT, ORGANIC ELECTROLUMINESCENT ELEMENT AND ELECTRONIC DEVICE |
JP2017135127A (en) * | 2014-04-21 | 2017-08-03 | 出光興産株式会社 | Organic electroluminescent element |
KR102577274B1 (en) * | 2015-11-16 | 2023-09-12 | 삼성전자주식회사 | Organic light emitting device |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040146744A1 (en) * | 2002-07-31 | 2004-07-29 | Satoshi Seo | Material for an electroluminescence element and electroluminescence element using the same |
WO2006081780A1 (en) * | 2005-02-04 | 2006-08-10 | Novaled Ag | Dopants for organic semiconductors |
US20080111484A1 (en) * | 2006-11-10 | 2008-05-15 | Kwon Do-Hyun | Organic light emitting display apparatus employing anode having multi-layer structure |
CN101222024A (en) * | 2007-01-11 | 2008-07-16 | 统宝光电股份有限公司 | System for displaying images |
CN101536608A (en) * | 2006-09-07 | 2009-09-16 | 法国圣-戈班玻璃公司 | Substrate for an organic light-emitting device, use and process for manufacturing this substrate, and organic light-emitting device |
Family Cites Families (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH11111463A (en) * | 1997-09-30 | 1999-04-23 | Sumitomo Chem Co Ltd | Organic elelctroluminescent element |
US6501217B2 (en) * | 1998-02-02 | 2002-12-31 | International Business Machines Corporation | Anode modification for organic light emitting diodes |
JP2001176673A (en) * | 1999-12-14 | 2001-06-29 | Tdk Corp | Organic electroluminescent element |
KR100493531B1 (en) | 2003-06-02 | 2005-06-07 | 한국전자통신연구원 | Formation method for anode of oxide film in organic electroluminescent device and organic electroluminescent device comprising anode of oxide film |
JP4461726B2 (en) * | 2003-07-16 | 2010-05-12 | ソニー株式会社 | ORGANIC LIGHT EMITTING ELEMENT, ITS MANUFACTURING METHOD, AND DISPLAY DEVICE |
DE10357044A1 (en) * | 2003-12-04 | 2005-07-14 | Novaled Gmbh | Process for doping organic semiconductors with quinonediimine derivatives |
US7030554B2 (en) * | 2004-02-06 | 2006-04-18 | Eastman Kodak Company | Full-color organic display having improved blue emission |
JP2005255889A (en) * | 2004-03-12 | 2005-09-22 | Toyo Ink Mfg Co Ltd | Material for organic electroluminescent element and organic electroluminescent element using the same |
US8188315B2 (en) * | 2004-04-02 | 2012-05-29 | Samsung Mobile Display Co., Ltd. | Organic light emitting device and flat panel display device comprising the same |
KR100573137B1 (en) * | 2004-04-02 | 2006-04-24 | 삼성에스디아이 주식회사 | Fluorene-based compound and organic electroluminescent display device using the same |
KR20060020156A (en) | 2004-08-31 | 2006-03-06 | 엘지.필립스 엘시디 주식회사 | Lcd device with low-resistance pixel electrode and fabricating methode thereof |
JP2006114544A (en) * | 2004-10-12 | 2006-04-27 | Chisso Corp | Organic electroluminescence element |
DE102005010979A1 (en) * | 2005-03-04 | 2006-09-21 | Technische Universität Dresden | Photoactive component with organic layers |
JP4378366B2 (en) * | 2005-08-04 | 2009-12-02 | キヤノン株式会社 | Light emitting element array |
KR100786291B1 (en) | 2005-10-24 | 2007-12-18 | 삼성에스디아이 주식회사 | Top-emitting OLED |
JP2007142022A (en) * | 2005-11-16 | 2007-06-07 | Seiko Epson Corp | Metal wiring and method of manufacturing same, thin film transistor, electro-optical device and electronic apparatus |
JPWO2007058172A1 (en) * | 2005-11-17 | 2009-04-30 | 出光興産株式会社 | Organic electroluminescence device |
JP4626526B2 (en) * | 2006-01-30 | 2011-02-09 | 株式会社デンソー | Organic EL panel and manufacturing method thereof |
EP1848049B1 (en) * | 2006-04-19 | 2009-12-09 | Novaled AG | Light emitting device |
US7879463B2 (en) * | 2006-05-10 | 2011-02-01 | Samsung Mobile Display Co., Ltd. | Dimethylenecyclohexane compound, method of preparing the same and organic light emitting device comprising the dimethylenecyclohexane compound |
KR101372850B1 (en) | 2006-05-10 | 2014-03-11 | 삼성디스플레이 주식회사 | Dimethylenecyclohexane compound, method for preparing the same and organic light emitting device comprising the same |
EP2031670B1 (en) * | 2006-06-22 | 2013-11-27 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device employing heterocycle-containing arylamine derivative |
EP2381743A1 (en) * | 2006-09-07 | 2011-10-26 | Saint-Gobain Glass France | Substrate for organic electroluminescent device, use and method for manufacturing said substrate, as well as an organic electroluminescent device |
JP2008098611A (en) | 2006-09-15 | 2008-04-24 | Kobe Steel Ltd | Display device |
JP4377906B2 (en) * | 2006-11-20 | 2009-12-02 | 株式会社コベルコ科研 | Al-Ni-La-based Al-based alloy sputtering target and method for producing the same |
JP2008145647A (en) | 2006-12-08 | 2008-06-26 | Sony Corp | Display device and method of driving the same |
US20080171128A1 (en) * | 2007-01-11 | 2008-07-17 | Gloria Cagampang | Storage stable creme filling fortified with omega-3 fatty acids |
JP4705062B2 (en) * | 2007-03-01 | 2011-06-22 | 株式会社神戸製鋼所 | Wiring structure and manufacturing method thereof |
KR100830318B1 (en) * | 2007-04-12 | 2008-05-16 | 삼성에스디아이 주식회사 | Light emitting display device and fabrication method for the same |
JP5301201B2 (en) | 2007-06-29 | 2013-09-25 | 株式会社ジャパンディスプレイウェスト | Display device, driving method thereof, and electronic apparatus |
JP2009076544A (en) * | 2007-09-19 | 2009-04-09 | Canon Inc | Organic el element |
KR100879477B1 (en) * | 2007-10-11 | 2009-01-20 | 삼성모바일디스플레이주식회사 | Organic light emitting device |
JP2009099636A (en) * | 2007-10-15 | 2009-05-07 | Hitachi Displays Ltd | Display device and method of manufacturing the same |
KR101457146B1 (en) | 2007-11-09 | 2014-10-31 | 주식회사 칸세라 | Preparation method of silicon carbide filter |
JP4611418B2 (en) * | 2007-12-26 | 2011-01-12 | 株式会社神戸製鋼所 | Manufacturing method of display device |
JP2008263248A (en) * | 2008-08-07 | 2008-10-30 | Sumitomo Electric Ind Ltd | Mounting member of semiconductor light-emitting element, and method of manufacturing the same |
KR101097315B1 (en) * | 2009-10-12 | 2011-12-23 | 삼성모바일디스플레이주식회사 | Organic light emitting device |
KR20110039810A (en) * | 2009-10-12 | 2011-04-20 | 삼성모바일디스플레이주식회사 | Organic light emitting device |
-
2009
- 2009-10-12 KR KR1020090096822A patent/KR101097316B1/en active IP Right Grant
-
2010
- 2010-10-06 EP EP10186689.5A patent/EP2309565B1/en active Active
- 2010-10-08 JP JP2010228945A patent/JP2011082172A/en active Pending
- 2010-10-12 US US12/902,315 patent/US8617721B2/en active Active
- 2010-10-12 CN CN201410182230.4A patent/CN103943784B/en active Active
- 2010-10-12 CN CN2010105130766A patent/CN102097594A/en active Pending
-
2014
- 2014-07-17 JP JP2014146901A patent/JP2014239048A/en active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040146744A1 (en) * | 2002-07-31 | 2004-07-29 | Satoshi Seo | Material for an electroluminescence element and electroluminescence element using the same |
WO2006081780A1 (en) * | 2005-02-04 | 2006-08-10 | Novaled Ag | Dopants for organic semiconductors |
CN101536608A (en) * | 2006-09-07 | 2009-09-16 | 法国圣-戈班玻璃公司 | Substrate for an organic light-emitting device, use and process for manufacturing this substrate, and organic light-emitting device |
US20080111484A1 (en) * | 2006-11-10 | 2008-05-15 | Kwon Do-Hyun | Organic light emitting display apparatus employing anode having multi-layer structure |
CN101222024A (en) * | 2007-01-11 | 2008-07-16 | 统宝光电股份有限公司 | System for displaying images |
Non-Patent Citations (1)
Title |
---|
TOSHIHIRO KUGIMIYA,ETC: "Anode Electrode of Al-Ni Alloy Film Directly in Contact with ITO for Top-Emitting OLEDs", 《SID 09 DIGEST》 * |
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CN103943784B (en) | 2016-08-24 |
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CN102097594A (en) | 2011-06-15 |
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